Hydrochloric Acid → HCID 67463124, compound

HRID 2043724Notes

Reaction equation

HRID 2043724 reaction equation
[CH3:1][N:2]([C@H:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1)[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[S:8][CH:9]=1)=[O:4].[ClH:33]>ClCCl.CO.O1CCOCC1>[ClH:33].[CH3:1][N:2]([C@H:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1)[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[S:8][CH:9]=1)=[O:4]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 674599981,1-dimethylethyl 4-[4-[(methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]carbonyl]-2-thiazolyl]-1-piperidinecarboxylate2×

Product 1

HCID 67463124HCID 67463124, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 4-[4-[(methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]-carbonyl]-2-thiazolyl]-1-piperidinecarboxylate (i.e. the product of Example 6, Step B) (2.4 g, 5.26 mmol) was dissolved in 20 mL of a mixture of dichloromethane and methanol (1:1), and 13.15 mL (52.6 mmol) of 1 N HCl in dioxane was added. The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The residue was dissolved in 20 mL of methanol and concentrated under reduced pressure (this procedure was repeated 3 times) resulting in 1.7 g of the title compound as a solid.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 20 mL of methanol
  4. concentrationconcentrated under reduced pressure (this procedure

Sources & evidence

ORD record
ord-d65c1d10bf4f4d5d95bb73dcedb4670f
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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